29 Winchester Street

Toronto, ON M4X 1A6 ( Cabbagetown-South St. James Town)

Quick Facts

Type: Fourplex

Style: 3-Storey

Size: Sq Ft

Age: Years

Taxes: $ 12,354 ( 2026)

Updated: 2026-07-20 16:26:30

Description

The finest 4-plex in Cabbagetown has returned to market for the first time in a generation! This impeccably maintained and professionally updated income property has been meticulously renovated and represents a rare opportunity to acquire a best-in-class asset of this stature in one of Toronto\'s most storied neighbourhoods. Over 4200+ sq ft of living space, complimented with multiple walk-out exterior spaces including 2x large private decks, a rear walk-out patio at grade, and a stunning oversized south facing rooftop terrace on the upper level overlooking lush rear grounds under a densely treed canopy. The building is home to a high-quality tenant base, and each suite enjoys dedicated climate controls. The building has been curated to appeal to professionals and offers living spaces that are ideal for both entertaining and relaxing in a quiet environment. Fine interior finishes include hardwood floors, updated bathrooms, updated kitchens, high ceilings, and large windows. Each unit has dedicated ensuite laundry. Parking is accessed via a private rear laneway off of Aberdeen Ave, including 4 parking spaces at present (of which 1 is a tandem parking space,) and the possibility exists to expand up to 6 car parking on site). 29 Winchester has been assembled to remain highly desireable and strongly appealing to tenants in any market. This premium location is steps to restos and shopping along Parliament Street, and accessible to multiple TTC options (including the Carlton Street Car) or a short walk to Castle Frank Station TTC Subway. Tenants can enjoy Winchester Park at their doorstep, or stroll to Riverdale farm. Mere minutes to the downtown core and Distillery District / St Lawrence Market. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.

Extras

Fourplex

Property

Status: For Sale

MLS #: C13578164

Price: $ 3,400,000

Address: 29 Winchester Street

Type:

Style: 3-Storey

Size: Sq Ft

Age: Years

Front On:

Taxes: $ 12,354

Tax Year: 2026

Lot Size:

Neighbourhood: Cabbagetown-South St. James Town

Nearest Intersection: Winchester & Parliament

City: Toronto

Postal Code: M4X 1A6

DOM: 52 Days

Last Update: 2026-07-20 16:26:30

 

Building

Interior

Bedrooms: 4

Bathrooms: 4

Rooms: 0

Kitchens: 4

Family Room:

Fireplace:

Basement: Apartment,

Central Vacuum:

 

Exterior

Exterior: Brick,

Driveway:

Garage: Lane Private Reserved/Assigned

Garage Spaces:

Parking Spaces: 4.00

Pool:

 

Utilities

Electricity (Hydro):

Gas:

Phone:

Cable TV:

Heat Type: Baseboard

Heat Source: Electric

Air Conditioning: Wall Unit(s)

Water:

Sewers:

 

Features

 

Rooms